Tetrahydroisoquinoline compounds

Abstract

Tetrahydroisoquinoline compounds represented by the formula: ##SPC1## In which X is a hydroxy group, Y is a hydroxy group or Y taken with X is --O--CH 2 --O--, Z is hydrogen or a hydroxy group, R 1 is hydrogen or an alkyl group of one to four carbon atoms, R 2 is hydrogen, an alkyl group of one to four carbon atoms or phenyl, pyrrolidinomethyl, piperidinomethyl, or morpholinomethyl, R 3 and R 4 each is an alkyl group of one to four carbon atoms or R 3 taken with R 4 and N is pyrrolidinyl, piperidino, morpholino, or 2-(1,2,3,4-tetrahydroisoquinolyl), and n is one or zero, Which compounds are effective as vasodilators, processes for the preparation of these compounds, and intermediate compounds useful in the preparation of such compounds.

We claim: 
     
       1. A compound having the structure: ##SPC18## ##SPC19## wherein   X is a hydroxy group and   Y is a hydroxy group, or   X taken with Y is a methylenedioxy group (--O--CH 2  --O--)   Z is hydrogen or a hydroxy group   R 1  is hydrogen or an alkyl group of one to four carbon atoms,   R 2  is hydrogen, an alkyl group of one to four carbon atoms, phenyl, pyrrolidinomethyl, piperidinomethyl, or morpholinomethyl,   R 3  and R 4  each is an alkyl group of one to four carbon atoms or R 3  taken with R 4  and N is pyrrolidinyl piperidino, morpholino, or 2-(1,2,3,4-tetrahydroisoquinolyl), and   n is one or zero.   
     
     
       2. A compound as set forth in claim 1 in which n is one. 
     
     
       3. A compound as set forth in claim 1 in which n is zero. 
     
     
       4. A compound as set forth in claim 1 in which X and Y each is a hydroxy group. 
     
     
       5. A compound as set forth in claim 1 in which X taken with Y is --O--CH 2  --O--. 
     
     
       6. A compound as set forth in claim 1 in which X and Y each is hydroxy,   Z, r 1  and R 2  each is hydrogen,   R 3  and R 4  taken with N is morpholino, and   n is one.   
     
     
       7. A compound as set forth in claim 1 in which X and Y each is hydroxy,   Z, r 1  and R 2  each is hydrogen,   R 3  and R 4  taken with N is 2-(1,2,3,4-tetrahydroisoquinolyl), and   n is one.   
     
     
       8. A compound as set forth in claim 1 in which X and Y each is hydroxy,   Z and R 1  each is hydrogen,   R 2  is methyl,   R 3  and R 4  taken with N is morpholino, and   n is one.   
     
     
       9. A compound as set forth in claim 1 in which X and Y each is hydroxy,   Z, r 1  and R 2  each is hydrogen,   R 3  and R 4  taken with N is piperidino, and   n is one.   
     
     
       10. A compound as set forth in claim 1 in which X, y and Z each is hydroxy,   R 1  and R 2  each is hydrogen,   R 3  and R 4  taken with N is morpholino, and n is one.   
     
     
       11. A compound as set forth in claim 1 in which X and Y each is hydroxy,   Z, r 1  and R 2  each is hydrogen,   R 3  and R 4  taken with N is morpholino, and   n is zero.   
     
     
       12. A compound as set forth in claim 1 in which X taken with Y is -O-CH 2  -O-,   Z, r 1  and R 2  each is hydrogen,   R 3  and R 4  taken with N is morpholino, and   n is one.   
     
     
       13. A pharmaceutically acceptable acid addition salt of the compounds set forth in claim 1.